#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/38/4313862.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4313862
loop_
_publ_author_name
'Louis S. Hegedus'
'Michael J. Sundermann'
'Peter K. Dorhout'
_publ_section_title
;
 Synthesis, Complexation, and Coordination Oligomerization of
 1,8-Pyrazine-Capped 5,12-Dioxocyclams
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4346
_journal_page_last               4354
_journal_paper_doi               10.1021/ic030090j
_journal_volume                  42
_journal_year                    2003
_chemical_formula_sum            'C34 H44 N8 O4'
_chemical_formula_weight         628.77
_chemical_name_common            'Pyrazine Capped Copper Cyclam'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.000(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.542(7)
_cell_length_b                   13.601(9)
_cell_length_c                   23.271(16)
_cell_measurement_reflns_used    5169
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      20.96
_cell_measurement_theta_min      1.09
_cell_volume                     3337(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_av_sigmaI/netI    0.0962
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15354
_diffrn_reflns_theta_full        23.48
_diffrn_reflns_theta_max         23.48
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            yellow/oran
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cubes
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.80
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.829
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         4823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.829
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0257P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0801
_reflns_number_gt                2668
_reflns_number_total             4823
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic030090j_3.cif
_cod_data_source_block           Complex5a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4313862
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.2799(3) 0.3717(2) 0.12400(13) 0.0655(9) Uani 1 1 d . . .
H1 H 1.1991 0.3585 0.1077 0.079 Uiso 1 1 calc R . .
C2 C 1.3839(3) 0.37156(18) 0.08985(12) 0.0557(8) Uani 1 1 d . . .
H2 H 1.3757 0.3570 0.0501 0.067 Uiso 1 1 calc R . .
C3 C 1.5019(3) 0.39237(17) 0.11252(13) 0.0516(8) Uani 1 1 d . . .
H3 H 1.5745 0.3929 0.0884 0.062 Uiso 1 1 calc R . .
C4 C 1.5140(2) 0.41235(16) 0.17014(12) 0.0464(7) Uani 1 1 d . . .
H4 H 1.5952 0.4274 0.1856 0.056 Uiso 1 1 calc R . .
C5 C 1.4079(2) 0.41070(16) 0.20625(12) 0.0370(6) Uani 1 1 d . . .
C6 C 1.2894(2) 0.39106(19) 0.18294(13) 0.0504(8) Uani 1 1 d . . .
C7 C 1.2004(3) 0.4046(2) 0.27176(14) 0.0730(10) Uani 1 1 d . . .
H7 H 1.1286 0.4039 0.2964 0.088 Uiso 1 1 calc R . .
C8 C 1.3197(2) 0.42146(17) 0.29604(11) 0.0430(7) Uani 1 1 d . . .
C9 C 1.3267(2) 0.43180(17) 0.36018(10) 0.0522(8) Uani 1 1 d . . .
H9A H 1.4157 0.4406 0.3727 0.063 Uiso 1 1 calc R . .
H9B H 1.2767 0.4894 0.3731 0.063 Uiso 1 1 calc R . .
C10 C 1.2186(2) 0.34806(16) 0.43981(10) 0.0330(6) Uani 1 1 d . . .
C11 C 1.3112(2) 0.38190(16) 0.48489(10) 0.0455(7) Uani 1 1 d . . .
H11A H 1.3922 0.3477 0.4796 0.068 Uiso 1 1 calc R . .
H11B H 1.2773 0.3671 0.5231 0.068 Uiso 1 1 calc R . .
H11C H 1.3244 0.4530 0.4812 0.068 Uiso 1 1 calc R . .
C12 C 1.1725(2) 0.24241(17) 0.45196(12) 0.0335(6) Uani 1 1 d . . .
C13 C 1.1068(2) 0.08634(16) 0.40326(10) 0.0344(6) Uani 1 1 d . . .
C14 C 1.1003(2) 0.05939(17) 0.33982(10) 0.0509(7) Uani 1 1 d . . .
H14A H 1.0483 0.1078 0.3194 0.076 Uiso 1 1 calc R . .
H14B H 1.0623 -0.0060 0.3356 0.076 Uiso 1 1 calc R . .
H14C H 1.1861 0.0590 0.3236 0.076 Uiso 1 1 calc R . .
C15 C 1.1977(2) 0.01763(16) 0.43418(11) 0.0517(8) Uani 1 1 d . . .
H15A H 1.2817 0.0218 0.4163 0.078 Uiso 1 1 calc R . .
H15B H 1.1662 -0.0500 0.4315 0.078 Uiso 1 1 calc R . .
H15C H 1.2038 0.0368 0.4747 0.078 Uiso 1 1 calc R . .
C16 C 0.97704(19) 0.08061(16) 0.43205(10) 0.0359(6) Uani 1 1 d . . .
H16A H 0.9457 0.0121 0.4298 0.043 Uiso 1 1 calc R . .
H16B H 0.9863 0.0978 0.4732 0.043 Uiso 1 1 calc R . .
C17 C 0.7613(2) 0.13545(16) 0.43426(10) 0.0358(6) Uani 1 1 d . . .
H17A H 0.7684 0.1587 0.4744 0.043 Uiso 1 1 calc R . .
H17B H 0.7373 0.0651 0.4352 0.043 Uiso 1 1 calc R . .
C18 C 0.6577(2) 0.19317(16) 0.40407(10) 0.0326(6) Uani 1 1 d . . .
C19 C 0.53176(19) 0.17486(17) 0.43345(10) 0.0448(7) Uani 1 1 d . . .
H19A H 0.4652 0.2127 0.4141 0.067 Uiso 1 1 calc R . .
H19B H 0.5373 0.1954 0.4737 0.067 Uiso 1 1 calc R . .
H19C H 0.5113 0.1046 0.4316 0.067 Uiso 1 1 calc R . .
C20 C 0.6932(2) 0.30283(17) 0.40629(11) 0.0335(6) Uani 1 1 d . . .
C21 C 0.8025(2) 0.43949(16) 0.35397(10) 0.0338(6) Uani 1 1 d . . .
C22 C 0.6941(2) 0.51384(16) 0.36091(10) 0.0482(7) Uani 1 1 d . . .
H22A H 0.6296 0.5018 0.3314 0.072 Uiso 1 1 calc R . .
H22B H 0.7275 0.5807 0.3567 0.072 Uiso 1 1 calc R . .
H22C H 0.6560 0.5065 0.3991 0.072 Uiso 1 1 calc R . .
C23 C 0.8582(2) 0.44645(17) 0.29358(9) 0.0489(7) Uani 1 1 d . . .
H23A H 0.9230 0.3956 0.2886 0.073 Uiso 1 1 calc R . .
H23B H 0.8966 0.5114 0.2882 0.073 Uiso 1 1 calc R . .
H23C H 0.7906 0.4369 0.2652 0.073 Uiso 1 1 calc R . .
C24 C 0.9017(2) 0.45909(15) 0.39952(10) 0.0362(6) Uani 1 1 d . . .
H24A H 0.9340 0.5270 0.3949 0.043 Uiso 1 1 calc R . .
H24B H 0.8617 0.4543 0.4379 0.043 Uiso 1 1 calc R . .
C25 C 1.1000(2) 0.41328(16) 0.44107(10) 0.0344(6) Uani 1 1 d . . .
H25A H 1.0586 0.4063 0.4790 0.041 Uiso 1 1 calc R . .
H25B H 1.1264 0.4828 0.4369 0.041 Uiso 1 1 calc R . .
C26 C 0.5646(2) 0.19103(17) 0.30973(10) 0.0416(7) Uani 1 1 d . . .
H26A H 0.5387 0.2583 0.3210 0.050 Uiso 1 1 calc R . .
H26B H 0.4897 0.1474 0.3125 0.050 Uiso 1 1 calc R . .
C27 C 0.6147(2) 0.19119(16) 0.24918(11) 0.0362(6) Uani 1 1 d . . .
C28 C 0.5340(2) 0.16564(16) 0.20358(12) 0.0435(7) Uani 1 1 d . . .
H28 H 0.4490 0.1482 0.2125 0.052 Uiso 1 1 calc R . .
C29 C 0.6923(3) 0.18939(17) 0.13870(11) 0.0425(7) Uani 1 1 d . . .
C30 C 0.7740(2) 0.21543(16) 0.18369(11) 0.0397(7) Uani 1 1 d . . .
C31 C 0.9005(2) 0.23940(18) 0.17040(12) 0.0550(8) Uani 1 1 d . . .
H31 H 0.9573 0.2575 0.2002 0.066 Uiso 1 1 calc R . .
C32 C 0.9421(3) 0.23675(18) 0.11449(14) 0.0617(9) Uani 1 1 d . . .
H32 H 1.0278 0.2526 0.1060 0.074 Uiso 1 1 calc R . .
C33 C 0.8595(3) 0.21102(19) 0.07008(12) 0.0610(9) Uani 1 1 d . . .
H33 H 0.8893 0.2098 0.0316 0.073 Uiso 1 1 calc R . .
C34 C 0.7371(3) 0.18778(17) 0.08156(11) 0.0538(8) Uani 1 1 d . . .
H34 H 0.6815 0.1704 0.0511 0.065 Uiso 1 1 calc R . .
N1 N 1.1826(2) 0.3897(2) 0.21676(11) 0.0820(9) Uani 1 1 d . . .
H1A H 0.877(3) 0.128(2) 0.3678(11) 0.098 Uiso 1 1 d . . .
N2 N 1.42234(18) 0.42557(13) 0.26453(9) 0.0417(5) Uani 1 1 d . . .
H2A H 0.7669(19) 0.2956(15) 0.3295(9) 0.050 Uiso 1 1 d . . .
N3 N 1.15734(17) 0.18720(13) 0.40530(9) 0.0325(5) Uani 1 1 d . . .
H3A H 1.1764(19) 0.2144(15) 0.3709(9) 0.039 Uiso 1 1 d . . .
N4 N 1.00809(18) 0.39054(13) 0.39669(8) 0.0348(5) Uani 1 1 d . . .
H4A H 0.9796(19) 0.3298(15) 0.4032(9) 0.042 Uiso 1 1 d . . .
N5 N 0.88395(18) 0.14531(14) 0.40621(8) 0.0368(6) Uani 1 1 d . . .
N6 N 0.75225(17) 0.33871(13) 0.35982(8) 0.0316(5) Uani 1 1 d . . .
N7 N 0.73303(18) 0.21645(13) 0.23983(9) 0.0409(5) Uani 1 1 d . . .
N8 N 0.5683(2) 0.16423(14) 0.14960(9) 0.0486(6) Uani 1 1 d . . .
O1 O 1.27527(13) 0.34337(10) 0.38349(6) 0.0380(4) Uani 1 1 d . . .
O2 O 1.14858(15) 0.21598(11) 0.50131(7) 0.0470(5) Uani 1 1 d . . .
O3 O 0.66989(15) 0.35000(11) 0.45027(7) 0.0461(5) Uani 1 1 d . . .
O4 O 0.66146(14) 0.15716(10) 0.34631(7) 0.0364(4) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.2(3) . . ?
C1 C2 C3 120.3(3) . . ?
C4 C3 C2 119.8(2) . . ?
C3 C4 C5 120.5(3) . . ?
N2 C5 C6 120.8(2) . . ?
N2 C5 C4 120.0(2) . . ?
C6 C5 C4 119.2(3) . . ?
N1 C6 C5 121.1(3) . . ?
N1 C6 C1 120.0(3) . . ?
C5 C6 C1 118.9(3) . . ?
N1 C7 C8 123.3(3) . . ?
N2 C8 C7 121.6(3) . . ?
N2 C8 C9 120.9(2) . . ?
C7 C8 C9 117.5(2) . . ?
O1 C9 C8 106.31(19) . . ?
O1 C10 C11 112.20(18) . . ?
O1 C10 C25 112.40(18) . . ?
C11 C10 C25 109.80(18) . . ?
O1 C10 C12 104.82(18) . . ?
C11 C10 C12 111.18(19) . . ?
C25 C10 C12 106.18(18) . . ?
O2 C12 N3 125.0(2) . . ?
O2 C12 C10 120.5(2) . . ?
N3 C12 C10 114.5(2) . . ?
N3 C13 C15 109.25(19) . . ?
N3 C13 C14 105.77(18) . . ?
C15 C13 C14 109.9(2) . . ?
N3 C13 C16 110.97(18) . . ?
C15 C13 C16 109.05(19) . . ?
C14 C13 C16 111.9(2) . . ?
N5 C16 C13 113.23(18) . . ?
N5 C17 C18 112.60(18) . . ?
O4 C18 C19 113.09(19) . . ?
O4 C18 C17 103.76(18) . . ?
C19 C18 C17 109.68(18) . . ?
O4 C18 C20 110.89(18) . . ?
C19 C18 C20 110.96(18) . . ?
C17 C18 C20 108.10(19) . . ?
O3 C20 N6 125.0(2) . . ?
O3 C20 C18 118.9(2) . . ?
N6 C20 C18 116.0(2) . . ?
N6 C21 C24 110.33(18) . . ?
N6 C21 C23 106.29(18) . . ?
C24 C21 C23 111.64(19) . . ?
N6 C21 C22 109.56(18) . . ?
C24 C21 C22 108.97(18) . . ?
C23 C21 C22 110.02(19) . . ?
N4 C24 C21 112.76(18) . . ?
N4 C25 C10 114.07(18) . . ?
O4 C26 C27 108.22(19) . . ?
N7 C27 C28 121.0(2) . . ?
N7 C27 C26 119.3(2) . . ?
C28 C27 C26 119.7(2) . . ?
N8 C28 C27 124.2(2) . . ?
N8 C29 C30 120.6(2) . . ?
N8 C29 C34 119.3(3) . . ?
C30 C29 C34 120.1(3) . . ?
N7 C30 C29 121.3(2) . . ?
N7 C30 C31 120.2(3) . . ?
C29 C30 C31 118.5(3) . . ?
C32 C31 C30 120.3(3) . . ?
C31 C32 C33 120.6(3) . . ?
C34 C33 C32 120.4(3) . . ?
C33 C34 C29 120.1(3) . . ?
C7 N1 C6 116.1(3) . . ?
C8 N2 C5 117.0(2) . . ?
C12 N3 C13 126.6(2) . . ?
C25 N4 C24 110.19(17) . . ?
C16 N5 C17 111.10(17) . . ?
C20 N6 C21 125.41(19) . . ?
C27 N7 C30 116.9(2) . . ?
C28 N8 C29 115.9(2) . . ?
C9 O1 C10 117.78(17) . . ?
C26 O4 C18 115.86(17) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.354(3) . ?
C1 C6 1.400(3) . ?
C2 C3 1.381(3) . ?
C3 C4 1.374(3) . ?
C4 C5 1.400(3) . ?
C5 N2 1.380(3) . ?
C5 C6 1.388(3) . ?
C6 N1 1.373(3) . ?
C7 N1 1.310(3) . ?
C7 C8 1.398(3) . ?
C8 N2 1.308(3) . ?
C8 C9 1.501(3) . ?
C9 O1 1.426(3) . ?
C10 O1 1.442(2) . ?
C10 C11 1.505(3) . ?
C10 C25 1.533(3) . ?
C10 C12 1.543(3) . ?
C12 O2 1.230(3) . ?
C12 N3 1.330(3) . ?
C13 N3 1.472(3) . ?
C13 C15 1.520(3) . ?
C13 C14 1.523(3) . ?
C13 C16 1.526(3) . ?
C16 N5 1.449(3) . ?
C17 N5 1.455(3) . ?
C17 C18 1.517(3) . ?
C18 O4 1.431(3) . ?
C18 C19 1.514(3) . ?
C18 C20 1.539(3) . ?
C20 O3 1.233(2) . ?
C20 N6 1.340(3) . ?
C21 N6 1.476(3) . ?
C21 C24 1.513(3) . ?
C21 C23 1.526(3) . ?
C21 C22 1.535(3) . ?
C24 N4 1.460(3) . ?
C25 N4 1.449(3) . ?
C26 O4 1.407(2) . ?
C26 C27 1.505(3) . ?
C27 N7 1.312(3) . ?
C27 C28 1.403(3) . ?
C28 N8 1.307(3) . ?
C29 N8 1.374(3) . ?
C29 C30 1.401(3) . ?
C29 C34 1.412(3) . ?
C30 N7 1.376(3) . ?
C30 C31 1.407(3) . ?
C31 C32 1.374(3) . ?
C32 C33 1.396(4) . ?
C33 C34 1.355(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4411106
